Anyone with a ton of disposable income can buy themselves a topnotch wardrobe…but does that really make you stylish? Not from what I’ve seen.
Style is more than arming yourself with the latest it-bag and slipping on the coolest shoes out there. It’s defining your personal style with confidence. I’ve seen it many times all over the place…people armed with hugely expensive designer pieces that don’t pair well with what they are wearing, women teetering on sky high Pigalles and looking like they hate every moment of it. That is not style, my friends.
Now, let me step off my soapbox for a minute and cop to the fact that I’ve been guilty myself of scouring Instagram and Pinterest for the latest styles and trends and buying the exact trendy items I find. There isn’t necessarily anything too wrong with that, except that expensive trendy items will go out of style inevitably, and you may be left with a pile of stuff you no longer wear that costs you a few car payments.
This is when you need to learn how to make nondescript items chic and cool, and best of all, your own. When you find something classic that you truly love, I feel the item looks even better, and I guarantee, you’ll have others asking where you got that awesome, enviable and covetable insert clothing item or accessory here.
So, with that, here are seven habits of the truly stylish to help you along with building that wardrobe to end all wardrobes.
1. They don’t surf street style blogs and copy exactly what they see.
Street style photos are a great source of fashion inspiration, but they are just that, inspiration. It’s unreasonable to see a picture of some wealthy fashion editor or socialite and run at full speed to the nearest Barney’s to buy her entire outfit. One must remember that some of these people have been given their clothing by large fashion houses as a marketing ploy to get us poor readers to buy them full price. Others are incredibly wealthy and it’s their job to waltz around the world being photographed in the latest drool-worthy styles.
It truly pays to draw inspiration from the glitterati and find pieces that have the same cool factor and jaw-dropping effect. One of my favourite pieces in my closet is a $5 kimono I bought at a fast-fashion retailer. Miraculously, it has held up extremely well, is cut beautifully for my frame, is so light, airy and floaty that is has the most beautiful movement when I walk and I get a million compliments on it.

2. They aren’t ashamed or afraid of any store – they can find something great almost anywhere
I am queen of this. I love my designer stores and high-end department stores, but I love my fast fashion retailers and cheesy teeny bopper stores too.
When nobody is looking, I slip into Forever 21 and load up on accessories by the dozen, cute socks, basic tees and tanks, and the ooccasional pair of awesome flat sandals that I know won’t wreck my feet. I have also scored great winter coats, beautiful scarves and sweaters at places like H&M, American Eagle Outfitters and a personal favourite – Garage Clothing.
You can also find some huge scores a thrift shops (my girlfriend scored an Arctic fox hat at Value Village – JEALOUS), and every now and then I’ll find gems at stores like Winners, Marshall’s and Century 21…the last one being a veritable treasure trove.
3. They style themselves according to their own taste.
Sometimes my head explodes when I ask a person where they found their beautiful scarf and they respond: “It’s a 50-yr-old vintage piece from this little hole in the wall I found in Toronto.” I’m looking at you, Erika.
My sister Erika is queen of styling. She finds random beautiful pieces at boutiques and vintage shops (you will rarely find her in a mall) and she styles them so beautifully, that I often find myself looking at her and thinking: “Jeez – I would have never thought to do that.”
She rolls up her skinnies, she rocks big leather belts with even bigger buckles (the OC Transpo belt being a totally weird and awesome favourite), she has the best collection of eclectic costume jewelry and she just racks up the compliments every time she sets foot outside.

4. They always look a little less “put together” than everyone else.
In a sea of ballgowns and updos, there will be the one super stylish girl rocking a slim-fitting tuxedo with Converse, or when everyone is swishing around their long, beachy waves, she’ll be swanning around with a pixie cut.
The super stylish just seem a little cooler than everyone else in whatever environment they’re in. My friend Katie is a wonderful example of this. In a sea of charm bracelets and mass-produced statement necklaces, Katie features her collection of gorgeous Jenny Bird jewelry that no one else seems to have. When everyone else is storming Kate Spade for purses, Katie will show up with her Fjällräven backpack. Yes – we plan on raiding her closet and yes – I’m stealing that totally awesome backpack!!
5. They know that labels don’t make them cooler.
All you need to be stylish is confidence. Look at Iris Apfel. She’s been kicking around for 93 years, strutting her stuff in some of the most outlandish outfits and incredible jewelry on Earth. Is she hounding some poor sales associate at Barney’s for a $3000 Céline bag they must have that will be out of style in a year? No.

You absolutely do not need to spend a mint on clothing and accessories to look cool. You can rock an old grey sweatshirt like this:

and still look wayyyyy better than this:

6. They aren’t slaves to fashion.
Some of the most stylish people are able to have fun with fashion and follow trends without looking like a slave. If you don’t like a trend—even if every blogger under the sun is wearing it—don’t buy into it. It’s that simple.
Hate fringe? That’s ok! Won’t be caught dead in culottes? Don’t worry – most people wouldn’t be!

7. They don’t dress to be considered stylish.
In the age that one barely remembers before blogs, Fashion Week and street style, many people dressed for themselves, the lives they led, their budgets and most of all, what looked good on them. Maybe we should get back to that…
If you can’t walk in them, don’t wear them. If buying that bag means that you’ll be eating ramen noodles for a month? DON’T BUY IT. If every single girl in your city owns it…pick something else! Develop your own style and be confident wearing it…like the guy I see dressed like a banana every now and then. ;o)

Anything to add? Let me know in the comments!
xo,
Love this!! It speaks to my heart!
PS: glad you FINALLY came around on the culottes.
Author
Ahahahaha!!! Thank you! I still keep my eyes open for a cute pair…but I assume that would be the same futile exercise as finding a flattering flatform sandal!
Great post!
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Thank you, Lety! xo
Awesome post!
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Thank you!!!
Great post! I don’t think being a slave to labels will in anyway make you more fashionable
Author
I agree. I guess a lot of people just equate some labels with great style. I just love originality. As great as labels are, do you really want to be a walking billboard for Gucci or Louis Vuitton?
Erika should do fashion posts on her IG!
Author
I agree, Joy! She loves to focus on healthy foods, fitness and yoga…trying to get her to do some style pics!! xo
LOL I kinda like that Paris pic! It’s too hilarious! *runs*
However, great post and I agree with much of it 🙂
Author
Haha! Hey – she’s sort of pretty in pink. I just can’t stand her. Thanks for reading, luv! xoxo
Yes, yes, yes, yes & yes. 🙂 I have a very well-defined sense of style that doesn’t change much year to year: billowy vintage micro-pleated skirts, nipped-waist jackets, sky-high heels and a LOT of thrifted pieces from the 50s and 60/ (especially tiny bags!!). My all-time favorite thrifted find was a beautifully seamed Dior vest from the 80s — winter white with a long row of military-style brass buttons. I think I paid $5 for it — no kidding!!
The older I get, the more confident I am in dressing for ME — I call my go-to style Ladylike Vintage, & while it’s not usually what fashion bloggers are wearing, it looks good on me, it makes me happy, & — as a byproduct of that — I know it makes other people happy too. 🙂
There are are so many interesting and creative and beautiful women out there — I’d love to see what we’d all look like if we just wore what we enjoyed wearing. 🙂 The world would probably be a more interesting place.
I truly love your posts, lady! You’re a breath of positivity and fresh air!
Author
Thank you so, so much. Your encouragement is so great! Wow – that Dior vest sounds like a dream. I agree with you. I find in small towns and big cities alike, everybody looks the same. It would be so great to see a bit more individuality, or just to know that more people are comfortable just being themselves! I think this especially with these televised award shows. Everyone looks so scrubbed and uber perfect…I miss the days of Cher showing up in crazy, feathered Bob Mackie, or Barbra Streisand wearing a see-through glittering jumpsuit with strategically placed hands on her lady parts! Lol! So much more fun! Thanks for reading! xoxoxo
You are SO right … & oh, those Bob Mackie creations … I’d completely forgotten how fun and fabulous they were! You made me smile. 🙂
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Thrilled to make you smile!! I really do miss the creativity and frankly, the fun of the over-the-top, nutso drama!!! Looking perfect like J.Lo is nice, but looking perfect in a halo of raven feathers is AWESOME! Haha! xo
YES. 🙂 Now I want a crown made of feathers, ha… Maybe I could at least pull off a fascinator or a feathered headband with a little birdcage veil. I like crazy fashion because it makes the reat of us ladies just a *little* bit braver. 😉
Author
Haha! Aww! I picked up a great fascinating in blush pink with a polka-dotted birdcage veil a few months ago!! I have no idea where I’m going to wear it, but just looking at it makes me happy! xo
I have a crush on that hat already. 🙂 When something is fabulous enough, you make an occasion. 😉
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Absolutely. It’s so fab, and I’m dying to give it a whirl, maybe I’ll wear it to the grocery store!! Lol!
Haha. I love it! I remember once when I was in high school, my friends and I decided to wear our prom dresses out to dinner just because. It was perfect. 🙂
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Haha! What a cute idea!
girl # 2 here! ☺️ thrift shop rules!
Absolutely LOVE this post and every single one of these habits and pointers are spot on! I think through the years the most valuable lesson I’ve learnt is learning to budget and really picking and choosing ONLY the trends and classic pieces that I can pair with atleast more then three outfits which are currently existing in my closet. Silly as it may sound .. but hey I have saved a fortune and my style has definitely improved.
Xo. http://www.sonamnaiducreative.com
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Fantastic advice which I agree with 1000%. Why waste money with garbage clothing?
LOVE this post..and my fur hat : )
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Haha! Thanks Erin! So stealing that hat from you! Lol! xo
yasss! all of these tips – my mom taught me all of these tips and she is super stylish. 🙂 Fashion should be fun, comfortable and make you happy – there’s no point if you put something on and feel like crap! You should be smiling when you put something on and that’s when you know it’s made for you!
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Exactly, Syah! Let’s hear it for all the stylish moms out there!! xoxo
I agree!! This is s great post. I’m all about being unique with your style. It’s cool to have a fashion icon but always be an individual.
Love this ^•^
I love this post! I completely agree with everything in this piece, especially about being stylish doesn’t mean you spend a pretty penny on an outfit or have designer brands wrapped around your body! xoxo, lauren 🙂
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Thanks so much – glad you liked it, Lauren! I’m a huge fan of working with what you have as opposed to spending tons on a great outfit…unless the piece is great and you really have to have it! LOL! xox